7 design leadership lessons I learnt the hard way

Quick tip; your skills will be irrelevant.

First, let me clear something out to you — the “lone wolf” thing is bullshit.

Trust me; I used to think of myself as one. 18 months of freelance UI design, plus another 18 months of being the only product designer in the office, means your brain will be wired to believe that anyway.

Early on, you’ll feel like you’re invincible; that every new skill is just a few tutorials and practice sessions away, that someone should just directly fund you because you get more done than the average startup, that specialisations and “doing just one thing well” is for chumps.

Enter scale.

That’s when you realise a bigger plate and a sharper fork doesn’t increase the limit to how much you can eat. At first, you blame it on lack of time — “if I had enough time, I’d do that myself too.” Then you blame it on lack of practice — “if I had tried this a couple of times before, I’d be doing this much better right now.” But a couple of other blame-shifts later, you eventually arrive at the endpoint; “I can’t do all of this by myself!”

Enter team.

Of course, you first treat them like shit. Accidentally of course; you’re not a bad person. It’s just that these people are basically extra hands who need to do as they’re told so that some of the workload is off your head. The first few people to leave are “not upto the job”; the next few “had different expectations”; but again, a couple of other blame-shifts later, you have the next revelation; “I’m pretty terrible at getting work done from other people.”

Enter leadership.

Congratulations; you’re now at level one of a whole new game, where none of your previous upgrades have any relevance. Your old skills were all for work; out here, you need people skills, and as a lone wolf, you have none.

It took me a whole year to figure out what I think are just the basics; but they’ll hopefully help you better understand the new mindset you need to be in on a day-to-day basis as a leader. If not, hey, they’ll at least help you make sense of all those cheesy leadership quotes all over the place.

Disclaimer; I work as a lead in a design agency, so a lot of it is written from that point of view; but IMHO, the basic points should hold true for literally any leadership role (unless it’s like a cult or something). Cheers!

1. Always have answers

Why wasn’t it delivered? How do you do this? How far are we in the project? What did the client say she wanted that day? Why is one of your team members not delivering quality work? Can I take leave? Who’ll do this task?

Answering everything is exactly what most people transitioning into leadership are not prepared for. Early-stage thoughts include “he didn’t work properly, what can I do about it?”, “how am I supposed to know this, you should know this”, and “that’s not my problem, is it?”. All very valid statements as an individual; all terrible answers as a leader.

You have to realise that what used to be your opinions on things are now directives for people. They look up to you to understand “what…”, “how…”, and “why…”, or look for you to explain “what didn’t…”, “how come…”, and “why not…”. You are answerable to anyone above you for anyone below you. You should know, and be able to tell, what is going on within your areas of responsibility at all times. “To be on top of things” is literally your new job.

If you are in an environment where you can influence this, make sure you increase your responsibilities gradually. Start with one or two projects, with one or two people, and slowly work your way up with the pressure. For those who didn’t get much say in the matter, however, here are some “quick tips” that’ll help you stay sane amidst the barrage of questions that are headed your way;

First, anticipate questions. Draw a line from that ugly client email to your boss going “why is this project broken again?”. Don’t wait for that struggling employee to come and ask you a question. Keep track of deadlines and see whether you’ll be able to make them or do you need to prepare for a possible delay. A lot of questions you dread will disappear with basic pre-emptive action, for which you only need to be aware of what’s going on and keep all high-level aspects of your projects on your fingertips.

Second, be specific. Your words will be interpreted incorrectly more often than you’d think. You might leave a lot of things out of your quick briefs as “obvious”, “understood”, or “you’ll get it once you read it/talk to them/work on it”. Most of these will come back to bite you. Explain in excruciating detail what you’re looking for, how your teammates should do it, and why they need to do it. Spend the extra minute; you’ll save everyone a lot of wasted hours.

Third, reply, don’t react. I’d have titled this “be patient”, but that advice doesn’t actually help me in the heat of things. What does help is just answering and getting it over with. Don’t attach emotions or prejudices to those answers. Don’t say “I’ve told you this before already”, “you should know this by now”, “isn’t that obvious”, or anything on those lines. Just give people the answer they’re looking for; it’s simpler for everyone.

And lastly, keep things moving. There will always be questions to which even you don’t have the answers. But a “what you should do next” is also equally productive. Give people a direction; tell them to talk to someone else, find out on the internet, ask the client directly (a thing that works wonders both for the project and the relationship), or try something out first and then get back to you.

The fun part about leadership comes when you realise that for a lot of questions, it doesn’t even matter what the answer is, as long as there is one. Both good and bad answers usually work better than no answers.

“A leader is one who knows the way, goes the way, and shows the way.”

- John C Maxwell

2. Never criticise in public

Some of your worst office memories will involve you being publicly embarrassed by a superior. Maybe they yelled at you, maybe they showed you how you performed a task terribly, maybe they handed out a taunt, or maybe they just casually assumed you weren’t capable. The important thing though, is that it was most likely public.

Once you become a leader, you’re going to be the person on the other side of this story. And people will fuck up because ultimately, they’re humans. And you’ll eventually notice that the part everyone focuses on is not the fuck-up itself or the person who fucked it up, but your response to the whole thing.

I will not lie — roasting someone’s incompetence in public is both highly tempting and highly gratifying, and I’ve done it several times. But it earns you no points. Your team members will start hiding mistakes from you out of fear, be less willing to offer you counsel, will avoid getting involved in anything but the bare minimum, and (ironically) deliver lower-quality output still. Oh, and they’ll bitch about you behind your back.

Not that any of these reasons will stop you from flipping out the next time; after all, you’re human too. So the next time you feel frustrated and ready to lash out at this teammate who had it coming, do something that is counter-intuitive but really works — instead of being a hard-ass, loosen up.

Remind yourself that deadlines are arbitrary, a few issues here and there aren’t the end of the world, and quality doesn’t magically appear out of nothing. By lowering the stakes, you lower the pressure itself, and then find yourself in a much more cooperative and supportive mindset. Basically, you just need to tell yourself “fine, it’s not that big of a deal”.

And when critique is necessary, take all offending team members into a room and show them where they’re lacking. Allow them to explain themselves; there is often is a good reason, which they’ll be more than willing to tell you if they feel they’re being heard rather than being cornered. An outburst doesn’t help anyone become better; it just makes your teammates heavy-headed in the short-term, and repeated outbursts will just send them away looking for other bosses in other jobs.

“A boss has the title. A leader has the people.”

- Simon Sinek

3. Stop doing and start teaching

Ever wondered how you became a leader in the first place? If it’s because you and your superiors thought you’re very skilled at your job and therefore should be able to lead others at that job, yeah you both fucked up. Skilled employees, especially Type-A personalities, often make terrible or mediocre managers, because as soon as they become team leads, one or more of the following things start happening;

• You’re still the most skilled, so you’ll struggle to leave the grunt work to others. You’ll end up doing some anyway, eating into the time you should’ve been spending managing the project, helping others, working on processes, or just organising things better.
• Your superiors will now assume that since you’re in charge, every team member’s skill level and output quality will match yours. In reality, you’re not able to actually do anything anymore, and their quality and skill level stays where it is, leading to an effective decrease in output quality.
• You’ve never found yourself justifying your “preferences”, style of working, or rules that you made up which you think have helped you become more skilled. So every time a team member asks you “why do you want me to do it like this?”, you’ll struggle to explain, give a half-assed answer, and then get frustrated at them anyway.
• You’re not going to like managing other people and being responsible for them, because you liked being responsible for the work itself. You’ll feel that all your team members should be their own managers, and that it’s their problem how they deliver what is needed from them.

Meanwhile, your teammates like you less, find you an abrasive and arrogant know-it-all, and (yes, this really happens) start leaving small things for you to fix yourself. Well I mean, you only said what took them three hours to do would’ve taken you thirty minutes. Now watch those thirty minutes keep coming back to you again and again.

This became one of my biggest problems when I transitioned into the role of a team lead — the distance from design work that I loved to do. I could no longer actually design anything; I had to watch others do it. They’d do it wrong, they’d not get what I was saying, they’d miss things, and for several months I spent my late evenings fixing their work and then chastised them the next morning for not having done it properly in the first place. Time (and burnout) eventually showed me that I couldn’t keep doing this anymore — and my team members weren’t exactly grateful to me for any of it.

As a leader, you must realise that for your team’s work to mirror your expectations, your knowledge needs to become their knowledge; your skill needs to become their skill. The worst mistake you can do as a skilled employee who became a leader is expecting your level of output from your team without first giving them the tools you have to produce that output. Sit with them and help them do their work; teach them what you know. Don’t continue to do things yourself; you’re helping no one there.

“Before you are a leader, success is all about growing yourself. When you become a leader, success is all about growing others.”

- Jack Welch

4. Show them “why”

Despite a lot of friction with my first few teammates early on, they eventually began respecting me. I’d attribute this to one thing more than anything else (since most of the other things I learnt pretty late anyway)— things changed when I actively began involving them in my decision-making process.

You see, from a distance, any and every one of your directives can be questioned; and early on, it’s hard not to take every “why are we doing this” as a challenge to your authority, especially if you’ve just moved into a leadership role. But if you find yourself even thinking “we should do this because I said so”, realise that the mistake is yours, and a simple one — you’re not showing them why they’re doing what they’re doing.

Bring them in on client meetings and CC them in email threads. Hell, ask them to handle a few. Bring them in the room when your boss asks you questions about how you’re handling the project. Show them instances of all the work you’ve done gone down the drain because you failed to do something properly.

To most people, even the thought of being answerable the way you are will frighten them. Show them a sample of what you deal with, and why you do what you do. Not only does that dispel their doubts on why they’re doing what they’re doing, but it also makes them respect you more.

I’ve seen empathy spark in my teammates as I share with them some issues I’ve been facing. They’ve seen me struggle to defend their shoddy work to a client, and feel bad about it. To make them understand the stakes, don’t just tell them about it; show it to them. Most people will trust you more after that, and a special few will even find ways to help you do your job better.

There is no way this can go wrong, which means there should be no reason for you to not do this.

“Great leaders don’t tell you what to do.

They show you how it’s done.”

5. Organise their work

As a leader, your focus should move away from the groundwork and onto the team and the projects themselves. Key aspects should always be at your fingertips — “who’s working on what today”, “how far are we in each project”, “what are the next deliverables and when are they due”, and “what issues are your team members facing currently”.

But these things can’t (and shouldn’t be) your team’s problem as well. It’s on you to let each one of your teammates know which problems they should be focusing on and to make sure no one is dealing with things beyond their ability or bandwidth. Balancing their workload is one of your most important responsibilities; and though it’s unlikely you’ll ever find yourself not overburdened with work, your team will truly appreciate you keeping things simple and prioritised for them.

Also, be smart and consider other factors as well, like when one of your team members said they were bored of doing the same task again and again and want to try something new, or when one of them struggled with the same task last time and would need more help or time to complete it this time around.

And finally, keep in mind that switching between tasks is quite detrimental to productivity; so try and keep one person working on a few tasks only, for projects that they’re familiar with. Always give everyone a cushion, in which a few hours of unproductive work doesn’t throw all your predictions off.

Remember, it doesn’t matter how well you organised your work if the rest of your team is running around disoriented and clueless until the last moment.

“Leaders must be close enough to relate, but far enough ahead to motivate.”

- John C Maxwell

6. Build their enthusiasm — and keep it going

As a designer, I know a hard truth — not all design work is pretty. Most of it is either boring from the start, or becomes so after the client sends it back for the fifth time saying “it’s still not quite there yet”. Dull work won’t make your team leave, but it will make them fall out of love with what they do on a day-to-day basis.

An unspoken, but necessary, part of your job is to keep your team’s enthusiasm high regardless of the crap they might be working on. To do this, you need to find ways to keep their creative spirits going even in downtime, and remind them of the success they are craving for in times of high pressure.

For design work, I usually give my team ideas on how to make things more interesting. I add unnecessary but playful creative constraints; I ask them to try out a new style or tool; I ask them to revisit their old work in a completely new light, and see what they would change in it now.

If there’s no work for them somehow, I give them a problem I’m tangentially (or directly) working on; or an interesting design resource to read/watch and learn something new; sometimes I hand them an entirely new (but totally fake) project to work on.

When you’re leading a team of creative people, your true test is keeping their morale high with non-creative work. Designers, especially newcomers, have a very glorified view of what their jobs would entail; and it’s important that you don’t shatter their vision, and instead show them how the mundane tasks they do are important to achieve that vision.

Remind designers of all the eyeballs that would eventually see their work, and most will immediately double their zeal on the task at hand; remind them of the litany of client expectations and red-tape they’ll have to go through, and they’ll just be waiting for the day to end so they can go back home and do something “more meaningful”.

“Leadership is inspiring people. The thing that keeps the trains running on time is management.”

7. Give them their space

“Space” means a lot of different things here. The first would be “creative space” — the freedom to imagine whatever they want. As unintuitive as it sounds, avoid giving your team creative design direction until it’s almost too late — let them explore, and see what they come up with. Impart your ideas only when they’re unable to come up with any, or your ideas seem better to you than theirs.

On that last part, what I’ve noticed being a leader is that your creative inputs are rarely challenged, which can be both a boon and a bane depending on the context. So do whatever you can to stimulate, rather than stifle, your team’s creativity with your own.

The second is “procedural space”; their freedom to choose how they do a task and when. Of course, you can’t afford to give them unlimited runway; on a higher level, the tasks and deadlines you give them should be taken as gospel. But how they do them, how they break it down, whether they show you a draft version before or after lunch, leave it to them to figure out. Basically, don’t micromanage their work.

Two easy ways to make sure you’re not doing this is to not impose anything (“let’s get back together after lunch and discuss the progress”), but rather ask everything (“by when can you get back to me with updates on this?”), and to be retroactive rather than active about how they’re working (instead of finding them in the middle of their day and saying “do it like this”, you sit down at the end of the day and ask “did you try this?”).

The third is what I call “trial-and-error space”, which is exactly what it sounds like. Give them the time they need to try something new or something more — especially if they’ve asked for it. Ask for three output variations instead of one, but low-quality instead of perfected. Account for delays when someone is working on something they’ve never done before. Set up a system that allows them to fail fast; where you can catch them when they’re going wrong and correct them early on, instead of seeing all their work in the end and finding 50 things wrong with it.

And last, but certainly the most important, “personal space”. Don’t expect that if you call them during off-hours and want a change done quickly, it’ll be done, or done perfectly. Segregate home and work for your team. It’s wise to remember that they’re salaried employees, and you don’t own them 24x7; it’s not their responsibility to pick up your phone at 9 pm on a Saturday and do whatever it is you’re asking of them. Respect them personally, and they’ll respect you professionally in return.

“The man who leads the orchestra must turn his back to the crowd and let the musicians take all the attention.”